Phenol → Methyl 3-(phenyl-methoxyphosphinyl)-2-chloropropionate

HRID 374246Notes

Reaction equation

HRID 374246 reaction equation
[C:1]1([P:7](=[O:12])([O:10][CH3:11])OC)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:13][C:14](=[CH2:19])[C:15]([O:17][CH3:18])=[O:16].C1(O)C=CC=CC=1>>[C:1]1([P:7]([O:10][CH3:11])([CH2:19][CH:14]([Cl:13])[C:15]([O:17][CH3:18])=[O:16])=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 6659Methyl 2-chloroacrylateHCID 75234Phosphonic acid, phenyl-, dimethyl ester

Product 1

HCID 15052091Methyl 3-(phenyl-methoxyphosphinyl)-2-chloropropionateYield 90.1%

Procedure

138 g of dimethyl phenylphosphonate are slowly added at 20° C. under nitrogen to a solution of 120.5 g of methyl 2-chloroacrylate and 94 g of phenol. After a reaction time of 3 hours at 70° C. phenetole is removed by vacuum distillation. The residue represents 267 g of crude product with a 93.0% purity, which corresponds to a theoretical yield of 90.1%.

Workup

  1. customAfter a reaction time of 3 hours at 70° C. phenetole is removed by vacuum distillation

Sources & evidence

ORD record
ord-3307f53977b44fc8a76ecf241fbf580d
Source dataset
uspto-grants-1992_11
Patent number
US05166385

Reaction notes

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